iPod
Everyone loves the iPod.
For a Mac user, this is a natural player to get - it integrates well with the system, iTunes looks and feels like a Mac app, and it probably works great (I don't have a Mac but from what I've read, this is the case).
If you're a Windows user, however, then the only reason to buy an iPod is because you like the look of it.
It's finicky about it's USB connection, doesn't sync with Windows Media Player, and iTunes is very much a Mac app looking like a fish out of water running on a PC.
For example, apparently the Macintosh calls delete "Clear". I right-click on a playlist and I want to delete it - every other Windows program calls the option to delete it "Delete", but iTunes calls it "Clear". This is probably intuitive if you're a Mac user where (probably) every app calls this function "Clear", but on a PC, it's "Delete". For a while I thought you couldn't delete a playlist, since I expected that Clear would leave it there but remove all the songs from it.
You can open the iPod as a drive and drop MP3s onto it, but apparently unless you do this with iTunes, the player doesn't recognize them. Again every other MP3 player lets you do this; but not the iPod. I guess they really want you using iTunes. Makes sense, since Apple gets their revenue from the music store, but I'm in Canada, where we can't use the Apple music store. I don't want to use iTunes.
I'm trying to get XPlay to work well; so far I'm having mixed luck. I'll post when I figure out whether it works well or not.